Being Uncomfortable

Approximating Humanity
3 min readApr 4, 2019

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I was asked an interesting interview question yesterday:

Tell me about a time you felt uncomfortable in the workplace and how you resolved it.

My mind rushed with many examples I could use in answering this question. I perpetually feel like an outsider, so there have been many occasions where I’ve felt uncomfortable. But one example came to mind most of all.

I was working for a startup as their only Inside Sales Representative. I discovered, qualified, and handed opportunities to the Account Executive, a douchebag we’ll call Jake. He was the complete opposite personality type of me, and I was struck by that from the moment I first met him. He was loud — and I mean LOUD — and in my estimation, slightly obnoxious. He was born to do sales, basically.

An opportunity came along that I had worked really hard on, and the CEO wanted to let me keep the opportunity to work to close rather than handing it off to Jake to close. This absolutely enraged Jake. I don’t know if he has control issues or what, but I am sure he saw this as a threat to his position as Account Executive. Someone more junior than him was being handed the same work as him. He couldn’t stand it.

He was the type who was always joking around, but one time he wrote me an email with the subject line “FUD” and it was a link to a cybersecurity article. He just used the subject line of “food” as a way to catch my attention as a food-loving fat person. Or so that’s how I took it. I was deeply offended by his probably harmless comment. Now he was making it personal. Not cool.

It came to blows when we were sent to a conference in DC together. I decided to ditch him and join a CISO client of mine at Gartner, since he offered me an extra ticket. I was determined to prove myself capable of being a salesperson independent of Jake, but I went about it in the wrong way. Because I’m so uncomfortable with confrontation, I went around him rather than working with him.

When we returned to the office after the conference, the first thing he said to me was:

I don’t think you should work here anymore.

My stomach sank. I had such high hopes for my time at this company, and here was someone trying to destroy any chance I had at advancing. I couldn’t understand why he had it out for me, but he was understandably upset that I had tried to go around him and didn’t discuss the best plan of attack with him before going after it myself.

We sat down and talked it out, and by some miracle I managed to do so without crying my eyes out. We decided that I should take the $230K deal because the CEO awarded it to me, and because Jake had a lot of other deals to work on closing. I learned how to communicate with him more effectively, even though he is very different from me and it was difficult for me to find common ground with him. It’s possible to get along with people you have nothing in common with, though — that’s the mark of a good professional.

I learned a lot from the experience about getting too big for my britches. I became overzealous about the possibility of closing a big deal and lost sight of the fact that I needed to maintain a harmonious relationship with my Account Executive to achieve my career goals. It wasn’t acceptable for me to decide on a best course of action without consulting him first — it wasn’t my decision to make as someone very junior in the company. I am so intelligent that sometimes I think I know more than people with a lot more experience than me. It’s a fatal flaw.

Sometimes I need to talk less and listen more.

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Approximating Humanity
Approximating Humanity

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